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There's a good chance when you buy music from the iTunes Store that the files that you download will be copy protected by Apple's FairPlay DRM system. It's a great system that protects the rights of the artist and publisher by making it difficult for the consumer to distribute copyrighted material. However, DRM can also be very restrictive by stopping you playing legally purchased music on your MP3 compatible hardware. So, what happens if you want to play your DRM'ed music on a non-iPod?

This tutorial will show you a way to produce DRM-free music that doesn't require any special software that you would normally need to buy. All you'll need is the iTunes software, and a blank CD (preferably a rewritable (CD-RW)).

Before we begin, check for any updates that are available for your iTunes installation, or download the latest version from the iTunes website。

Configuring iTunes to burn and rip an audio CD

CD Burner Settings: In order to set up the iTunes software to burn an audio CD, you first need to go into the settings menu and select the correct disc format. To do this, click on the Edit tab on the main menu and select Preferences from the menu list. On the preferences screen, select the Advanced tab, followed by the Burning tab. First, make sure your CD burner is selected from the drop-down menu alongside the CD Burner option. Next, Select audio CD as the disc format that is to be written by your CD drive.

CD Import Settings: While you are still in the preferences menu, click on the Importing tab to access the CD ripping settings. Verify that the On CD Insert option is set to Ask to Import CD. Next, set the Import Using option to a format of your choice; the MP3 Encoder is your best choice if you want to import audio CDs as MP3 files that play on virtually all compatible devices. Choose an encoding bitrate from the Setting option; 128Kbps is the normal setting that is good enough for the average listener. And finally, make sure the Automatically Retrieve CD Track Names From Internet and Create File Names With Track Numbers and both checked. Click the OK button to save your settings.

Making a custom playlist

To be able to burn your DRM copy protected songs to audio CD you will need to make a custom playlist (File > New Playlist). You can add music tracks to a playlist easily by dragging and dropping them from your music library to your newly created playlist. For instructions on how to achieve this, why not follow our tutorial on How to Create a Custom Playlist Using iTunes.

While creating a playlist, make sure that the total playing time (displayed at the bottom of the screen) doesn't exceed the capacity of the CD-R or CD-RW you are using; typically, the total playing time of a 700Mb CD is 80 minutes.

Burning an Audio CD Using a Playlist

Once you have created a playlist, simply left-click it (located under the playlists section in the left pane), and then click on the File tab on the main menu, followed by Burn Playlist to Disc. The CD drive tray should now automatically eject so you can insert a blank disc; ideally use a rewriteable disc ( CD-RW) so you can reuse it multiple times. Before iTunes starts burning the DRM protected songs, it will remind you that creating an audio CD is for your own personal use only; once you have read this notice, click on the Proceed button to start burning.

Ripping an audio CD

The final step in this tutorial is to import (rip) the songs that you burned onto audio CD, back to digital music files. We have already configured iTunes (step 1) to encode any audio CD that is inserted into the CD drive as MP3 files and so this stage of the process will be mostly automatic. To start ripping your audio CD, simply insert it into your CD drive and click the Yes button to start. For a more in-depth look at this process, read the tutorial on How to Import CD Tracks Using iTunes.

Once this stage is complete, all the files that have been imported into your music library will be free from DRM; you will be able to transfer them to any device that supports MP3 playback.

Note:The only downside in using this method is that if you have a lot of
files that you need to convert, then it ends up a slow and tedious
process. With this in mind, use a legal drm removal tool if you have a
large quantity that you need to convert.

Maybe iTunes don't want your burning their music. I'm not sure cuz I don't use Itunes, but if it works on others that sounds like it might be the problem.

Here I found the below on Apple's site.

Symptoms
Find out what to do if you can't burn an audio CD using iTunes for
Windows. Sometimes an audio disc may not burn as expected. Here are some
things to check.
Resolution
Update iTunes
Download and install the latest version of iTunes for Windows.
Songs not authorized
iTunes will stop burning a disc if one or more of the songs in a
playlist were purchased from the iTunes Store but are not authorized to
play on this computer. This message appears:

"Some of the files can not be burned to an audio CD. Do you
still want to burn the remainder of this playlist? For more information
on why some files can not be burned, click below".

There's more so click the link below and see why you can't burn your cd.

Backing up your iTunes library to a CD or DVD To burn a CD
(CD-R or CD-RW), your computer must have a compatible CD burner. To burn
a DVD (DVD-R or DVD-RW), your computer must have a compatible DVD
burner. Check in iTunes Preferences to see if a drive is compatible. See
below for steps.To create your backup disc

Choose File > Library >Back up to Disc.

Select the option you want from the resulting dialog and click Back Up.

The two options you can select from are:

Back up entire iTunes library and playlists

Back up only iTunes Store purchases

Whichever
of these two options you choose, note that you can also choose "Only
back up items added or changed since last backup" to perform an
incremental backup.

Insert a blank disc (CD or DVD) into your computer's optical drive. iTunes will scan the disc and begin burning.

Note:
If the disc you insert does not have enough space to hold all of the
content you will be backing up, a dialog will appear asking whether you
wish to backup to multiple discs. You can click Data Discs to continue.

iTunes
burns the number of items that fit on one disc and then asks you to
insert subsequent discs to continue burning the remaining files. Don't
eject a disc while a backup is in progress. Spoken programs purchased from the Audible.com website are not backed up. Discs you create using the iTunes backup feature can be used only to restore; they can't be played in a CD or DVD player.

Restoring from a backup disc

Open iTunes.

Insert your backup disc.

iTunes will ask whether you want to restore from this disc. Click Restore.

What OS and burn software are you using? Can you see the music files when you look at the file explorer on the computer (My Computer or Computer in Windows and double click on the optical drive)? Check if the disc has any scratches.

If you see the music listed on the optical disc, check if the disc was finalized. (Again in Windows Computer, right click on the optical drive and it should be an option if the disc hasn't been finalized.)

If there are no files on the CD-R, make certain that the disc isn't being formatted before you try the burn. (Formatting should only be done on R/W discs.)

If the music files are on the optical disc and the disc was finalized, your CD player is not tracking across the disc properly. Try a lens cleaner. It may need repair and I've never successfully repaired a CD drive (the only ones I've had fail were in computers and were cheaper to replace). The mirror and the belt are the most likely places to have issues.

The
Wave® music system is designed to play commercial CDs, CD-Rs,
MP3-encoded CDS and CD-RWs. If your system has trouble playing MP3 CDs,
make sure the discs were recorded with compatible formats. See Cannot play MP3 CDs

The system may not be able to play certain CD-RW discs. Playability
is dependant on how the disc was recorded, including the format it was
recorded in and the actual disc used for recording. Note: iTunes
defaults to AAC as the encoding format. In order to use iTunes to make
CDs that will play on the Wave® music system, you’ll need to change the
format to MP3 How to Choose Import Options

Different brands of CD-Rs and CD-RWs use different materials which
may affect the ability of a player to read them. If you are burning
your own CD-Rs or CD-RWs, experiment with different brands of discs

If a commercial disc won’t play, check for scratches, fingerprints
or other physical damage. Try the CD in another player. If it still
won’t play, there may be a problem with the disc

Reset the system by disconnecting the power cord from the wall for one minute, then plug the system back in

Apparently a common error; if you google error 4280 you'll get several different versions of what is happening. Some blame the Sony CD's other blame Dell, HP, etc...like I said there is a long list so I didn't want to pick out just one, it depends on your Computer type, combined with the CDs..so go ahead and take a look. Personally from reading some of the fixes I came up with; don't use Sony disc and run at 16x to get rid of the error. Hope this helps..

I had the same promblem. What you should do is make a serperate file on you desktop and drag all of your music that you burn or download to that folder first. Drag it to Itunes after that. Now, you only have to drag the songs to Itunes if you want them on there for you iPod. Take the songs from the folder, and drag them to windows media players burn list. Insert a blank disc and you should be good. Keep in mind that you can only do this if you put downloaded or burned music to the created folder first. If you take it to Itunes first, you will have to re-download or re-burn your music again.
Hopefully this helped you guys.